So I was discussing this with Sno the other night: it's no secret that The Simpsons has become increasingly played-out and desperate over the years and only continues to exist due to a combination of increasingly hackneyed gimmicks (look forward to the death of a mystery character plus Family Guy and Futurama crossovers this fall!), the complacency of Neilsen families, and sheer momentum akin to that of a corpse being rolled into a ditch. But what is the definitive nadir of the series? The single worst moment; be it the moment most characteristic of the show's faults, the point of no return for the way its characters developed into hollow two-dimensional caricatures of themselves, or simply the most tasteless and conspicuous marketing ploy. I encourage discussion, but open by nominating a few examples:
Lisa the Simpson
I choose to open with the potentially controversial choice of an episode from the tail end of the Classic Era of the show, but I feel its an exemplary example of the way the show would perform character assassinations and then codify their replacements as the real deal, Invasion of the Body Snatchers style. This episode had potential as a story about Lisa growing as a person, or learning to be more tolerant of her less intellectual family, or overcoming a frustrating rut in her life. Instead, Lisa learns nothing and is told, in very matter-of-fact terms, that she is genetically superior to the rest of her family. Let that sink in a bit. Since this episode aired, every time Lisa -who has traditionally been the writers' liberal soapbox character- has a difference of opinion with anyone in her family, it's presented with the understanding that Lisa is naturally always right and that her family is naturally always wrong. On top of just making her plain preachy and annoying, she's been robbed of the ability to learn or grow from failure or ceasefire the way she did in, say, Lisa's Rival or Lisa the Vegetarian.
Treehouse of Horror XXII
Treehouse of Horror has become almost a seperate entity from the show itself, always garnishing significantly higher ratings than the rest of the season since even the most jaded fan will usually tune in out of sheer morbid curiosity (myself included). Naturally, like the main show, TOH has also gone downhill and drifted ever further away from its roots, with this being perhaps the most distant from the core concept of TOH. The episode is divided into three parody shorts based on parodies of the likes of The Diving Bell and the Butterfly, Dexter, and Avatar; which, as you may notice, are not even remotely Halloween or horror-related AT ALL. There's also an overly-long intro sequence based on 127 Hours and the first short quickly devolves into a half-baked Spider-Man sketch. The thing about parody is that you have to choose source material that's either extremely timely or has been accepted into cultural canon, and you have to be on the nose. This does neither. The chosen sources for each sequence were well past their sell-by date (127 Hours had come out a year previous, Avatar 2 years, and TDBATB and Dexter about half a decade) but weren't old or memorable enough to be considered classics, and there's a flagrant lack of understanding of the material that makes it irritating for anyone who's seen it and boring for anyone who hasn't. The TDBATB sequence loses steam halfway through and turns into Spider-Man (because we all remember the Turn Off the Dark injuries, right?) once the writers realize they can't squeeze blood from a stone.
Double Double, Boy in Trouble
"And did someone say 'long lost triplets?'"
I don't even have anything to say about this one. I think that promo art speaks for itself. This isn't the first time that a deliberately bad episode premise was joked about in a previous season and then made reality, either. See also: Moe getting a cell phone, Selma marrying Grandpa Simpson, and robot Marge
The Tik Tok Couch Gag
Apart from the shameless Top Fourty sycophanty and network interference (this originally aired during a special "music week" on FOX where every show would have a musical guest or sequence), here we have a prime example of modern Simpsons' complete and utter lack of understanding of who its characters are and what they stand for. Take a look at which characters they chose to lip-sync for the sequence: Lisa, Groundskeeper Willie, Principal Skinner and Superintendent Chalmers, Mr. Largo, Otto, Nelson, Moe, Marge, Comic Book Guy... None of these characters should have any interest in a vapid pop song about partying. Like, at all. These characters you love are dead, and now you get to see their corpses puppeted around Weekend at Bernie's style to sell iTunes downloads.
In conclusion, The Simpsons is a land of contrast. Thank you.